NP-MRD: Showing NP-Card for Ichanexic acid (NP0086227)

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Record Information

Version

2.0

Created at

2022-04-29 06:34:21 UTC

Updated at

2022-04-29 06:34:21 UTC

NP-MRD ID

NP0086227

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ichanexic acid

Description

Ichanexic acid is found in Citrus aurantium .

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292208342D          

 39 44  0  0  1  0            999 V2000
   -0.5885   -3.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0302   -2.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7894   -2.5351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326   -1.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5252   -1.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6198   -0.4071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0426    0.0847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1372   -0.7349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769   -0.0792    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2823   -0.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393   -0.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7964   -0.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8911    0.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286    1.0681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9817    1.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4715    0.7403    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5662    1.5599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8091    1.2321    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4813    1.9891    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0520    0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6104    1.3960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6481    0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4052    1.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0676    0.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9730   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2159   -0.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5535    0.0847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1337   -0.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6354   -0.5710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7428    1.7238    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4998    2.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2569    2.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1720    2.8087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8277    1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803    2.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3232    1.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6608    2.3794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1935   -1.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9413   -1.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  6  8  1  1  0  0  0
  6  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  1  0  0  0
 25 29  2  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 14 36  1  0  0  0  0
 36 37  2  0  0  0  0
  5 38  2  0  0  0  0
  2 38  1  0  0  0  0
  4 39  2  0  0  0  0
M  END


  Mrv1652304292208342D          

 39 44  0  0  1  0            999 V2000
   -0.5885   -3.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0302   -2.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7894   -2.5351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326   -1.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5252   -1.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6198   -0.4071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0426    0.0847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1372   -0.7349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769   -0.0792    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2823   -0.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393   -0.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7964   -0.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8911    0.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286    1.0681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9817    1.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4715    0.7403    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5662    1.5599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8091    1.2321    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4813    1.9891    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0520    0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6104    1.3960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6481    0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4052    1.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0676    0.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9730   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2159   -0.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5535    0.0847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1337   -0.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6354   -0.5710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7428    1.7238    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4998    2.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2569    2.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1720    2.8087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8277    1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803    2.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3232    1.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6608    2.3794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1935   -1.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9413   -1.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  6  8  1  1  0  0  0
  6  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  1  0  0  0
 25 29  2  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 14 36  1  0  0  0  0
 36 37  2  0  0  0  0
  5 38  2  0  0  0  0
  2 38  1  0  0  0  0
  4 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086227

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12O[C@@]11[C@@](C)(CCC3C4(COC(=O)C[C@H]4O)[C@@H](CC(=O)[C@]13C)C(C)(C)O)[C@@]([H])(OC2=O)C1=CC(O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O11/c1-22(2,33)13-8-14(27)24(4)12(25(13)10-34-16(29)9-15(25)28)5-6-23(3)18(11-7-17(30)35-20(11)31)36-21(32)19-26(23,24)37-19/h7,12-13,15,17-19,28,30,33H,5-6,8-10H2,1-4H3/t12?,13-,15+,17?,18-,19-,23-,24+,25?,26+/m0/s1

> <INCHI_KEY>
GNHQKMSKORXBRT-OGECFXSASA-N

> <FORMULA>
C26H32O11

> <MOLECULAR_WEIGHT>
520.531

> <EXACT_MASS>
520.19446185

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
0.0

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2'S,4R,5'R,10'S,11'R,14'R)-4-hydroxy-11'-(5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0^{1,14}.0^{2,7}]pentadecane]-3',6,13'-trione

> <ALOGPS_LOGP>
0.59

> <JCHEM_LOGP>
0.23651697933333118

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.213961858677454

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.778209817969826

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7874983239571574

> <JCHEM_POLAR_SURFACE_AREA>
169.18999999999997

> <JCHEM_REFRACTIVITY>
121.25109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2'S,4R,5'R,10'S,11'R,14'R)-4-hydroxy-11'-(5-hydroxy-2-oxo-5H-furan-3-yl)-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0^{1,14}.0^{2,7}]pentadecane]-3',6,13'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -1.099  -5.689   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.056  -4.556   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.473  -4.732   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.114  -3.332   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.980  -2.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.157  -0.760   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.080   0.158   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0      -0.256  -1.372   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0       2.570  -0.148   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.394  -1.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.807  -1.066   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.220  -0.454   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.397   1.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.160   1.994   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.699   3.463   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.747   1.382   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.924   2.912   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.510   2.300   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       0.898   3.713   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       0.097   1.688   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.139   2.606   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.810   1.688   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.223   2.300   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.460   1.382   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.283  -0.148   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.870  -0.760   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.633   0.158   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.850  -1.168   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      10.519  -1.066   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.986   3.218   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.400   3.830   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.813   4.442   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.788   5.243   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.012   2.416   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.750   4.136   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.337   3.524   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.100   4.442   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.361  -3.046   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.624  -3.027   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   39                                                  
CONECT    5    4    6   38                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6   20                                                       
CONECT    8    6                                                            
CONECT    9    6   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15   16   36                                             
CONECT   15   14                                                            
CONECT   16   14    9   17   18                                             
CONECT   17   16   18                                                       
CONECT   18   16   17   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    7   21                                                  
CONECT   21   20                                                            
CONECT   22   13   23   27   30                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27                                                            
CONECT   29   25                                                            
CONECT   30   22   31   35                                                  
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31                                                            
CONECT   35   30   36                                                       
CONECT   36   35   14   37                                                  
CONECT   37   36                                                            
CONECT   38    5    2                                                       
CONECT   39    4                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₁

Average Mass

520.5310 Da

Monoisotopic Mass

520.19446 Da

IUPAC Name

(1'R,2'S,4R,5'R,10'S,11'R,14'R)-4-hydroxy-11'-(5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0^{1,14}.0^{2,7}]pentadecane]-3',6,13'-trione

Traditional Name

(1'R,2'S,4R,5'R,10'S,11'R,14'R)-4-hydroxy-11'-(5-hydroxy-2-oxo-5H-furan-3-yl)-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0^{1,14}.0^{2,7}]pentadecane]-3',6,13'-trione

CAS Registry Number

Not Available

SMILES

[H][C@@]12O[C@@]11[C@@](C)(CCC3C4(COC(=O)C[C@H]4O)[C@@H](CC(=O)[C@]13C)C(C)(C)O)[C@@]([H])(OC2=O)C1=CC(O)OC1=O

InChI Identifier

InChI=1S/C26H32O11/c1-22(2,33)13-8-14(27)24(4)12(25(13)10-34-16(29)9-15(25)28)5-6-23(3)18(11-7-17(30)35-20(11)31)36-21(32)19-26(23,24)37-19/h7,12-13,15,17-19,28,30,33H,5-6,8-10H2,1-4H3/t12?,13-,15+,17?,18-,19-,23-,24+,25?,26+/m0/s1

InChI Key

GNHQKMSKORXBRT-OGECFXSASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus aurantium	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.59	ALOGPS
logP	0.24	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.78	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	169.19 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	121.25 m³·mol⁻¹	ChemAxon
Polarizability	0 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for Ichanexic acid (NP0086227)

MOL for NP0086227 (Ichanexic acid)

3D MOL for NP0086227 (Ichanexic acid)

3D SDF for NP0086227 (Ichanexic acid)

3D-SDF for NP0086227 (Ichanexic acid)

PDB for NP0086227 (Ichanexic acid)

3D PDB for NP0086227 (Ichanexic acid)

SMILES for NP0086227 (Ichanexic acid)

INCHI for NP0086227 (Ichanexic acid)

Structure for NP0086227 (Ichanexic acid)

3D Structure for NP0086227 (Ichanexic acid)